Photosensitive resin composition, oxime sulfonate compound, method for forming cured film, cured film, organic EL display device, and liquid crystal display device

Abstract

Disclosed is a photosensitive resin composition comprising: (Component A) an oxime sulfonate compound represented by Formula (1); (Component B) a resin comprising a constituent unit having an acid-decomposable group that is decomposed by an acid to form a carboxyl group or a phenolic hydroxy group; and (Component C) a solvent wherein in Formula (1) R 1 denotes an alkyl group, an aryl group, or a heteroaryl group, each R 2 independently denotes a hydrogen atom, an alkyl group, an aryl group, or a halogen atom, Ar 1 denotes an o-arylene group or an o-heteroarylene group, X denotes O or S, and n denotes 1 or 2, provided that of two or more R 2 s present in the compound, at least one denotes an alkyl group, an aryl group, or a halogen atom.

What is claimed is: 
     
       1. A photosensitive resin composition comprising:
 (Component A) an oxime sulfonate compound represented by Formula (1); 
 (Component B) a resin comprising a constituent unit having an acid-decomposable group that is decomposed by an acid to form a carboxyl group or a phenolic hydroxy group; and 
 (Component C) a solvent 
 
       
         
           
           
               
               
           
         
       
       wherein in Formula (1) R 1  denotes an alkyl group, an aryl group, or a heteroaryl group, each R 2  independently denotes a hydrogen atom, an alkyl group, an aryl group, or a halogen atom, Ar 1  denotes an o-arylene group or an o-heteroarylene group, X denotes O or S, and n denotes 1 or 2, provided that of two or more R 2 s present in the compound, at least one denotes an alkyl group, an aryl group, or a halogen atom. 
     
     
       2. The photosensitive resin composition according to  claim 1 , wherein Component B above further comprises a constituent unit derived from at least one compound selected from the group consisting of a styrene derivative, a maleimide derivative, (meth)acrylic acid, and a hydroxy group-containing (meth)acrylate compound. 
     
     
       3. The photosensitive resin composition according to  claim 1 , wherein Component B above further comprises a constituent unit having a functional group that can react with a carboxyl group or a phenolic hydroxy group to form a covalent bond. 
     
     
       4. The photosensitive resin composition according to  claim 1 , wherein the acid-decomposable group is a group represented by Formula (Ia), Formula (Ib), Formula (IIa), or Formula (IIb) 
       
         
           
           
               
               
           
         
       
       wherein in the Formulae R 3  denotes an alkyl group or a cycloalkyl group, R 4  denotes an alkyl group, R 3  and R 4  may form a ring, R 5  denotes a tertiary alkyl group, R 5′  denotes a tertiary alkyl group or a tert-butoxycarbonyl group, Ar 2  and Ar 3  independently denote a divalent aromatic group, and a wavy line portion denotes the position of bonding to another structure. 
     
     
       5. The photosensitive resin composition according to  claim 1 , wherein Component A above is an oxime sulfonate compound represented by Formula (2), Formula (3), or Formula (4) 
       
         
           
           
               
               
           
         
       
       wherein in Formula (2) to Formula (4) R 1  denotes an alkyl group, an aryl group, or a heteroaryl group, each R 2  independently denotes a hydrogen atom, an alkyl group, an aryl group, or a halogen atom, each R 6  independently denotes a halogen atom, an alkyl group, an alkyloxy group, a sulfonic acid group, an aminosulfonyl group, or an alkoxysulfonyl group, X denotes O or S, n denotes 1 or 2, and m denotes an integer of 0 to 6, provided that of two or more R 2 s present in the compound, at least one is an alkyl group, an aryl group, or a halogen atom. 
     
     
       6. The photosensitive resin composition according to  claim 1 , wherein Component A above is an oxime sulfonate compound represented by any one of Formulae (5) to (10) below 
       
         
           
           
               
               
           
         
       
       wherein in Formulae (5) to (10) R 1  denotes an alkyl group, an aryl group, or a heteroaryl group, R 2  denotes a hydrogen atom, an alkyl group, an aryl group, or a halogen atom, each R 6  independently denotes a halogen atom, an alkyl group, an alkyloxy group, a sulfonic acid group, an aminosulfonyl group, or an alkoxysulfonyl group, R 7  denotes an alkyl group, an aryl group, or a halogen atom, R 8  denotes a hydrogen atom or a methyl group, R 9  denotes a hydrogen atom, an alkyl group, or an aryl group, X denotes O or S, and m denotes an integer of 0 to 6, provided that in Formula (6), Formula (8), and Formula (10), not all of R 2 , R 8 , and R 9  are hydrogen atoms. 
     
     
       7. The photosensitive resin composition according to  claim 1 , wherein Component A above is an oxime sulfonate compound represented by any one of Formulae (11) to (16) below 
       
         
           
           
               
               
           
         
       
       wherein in Formulae (11) to (16) R 1  denotes an alkyl group, an aryl group, or a heteroaryl group, R 8  denotes a hydrogen atom or a methyl group, R 10  denotes a hydrogen atom or a bromine atom, R 11  denotes an unsubstituted alkyl group having 1 to 8 carbons, a halogen atom, a chloromethyl group, a bromomethyl group, a bromoethyl group, a methoxymethyl group, a phenyl group, or a chlorophenyl group, R 12  denotes a hydrogen atom, a halogen atom, a methyl group, or a methoxy group, R 13  denotes an unsubstituted alkyl group having 1 to 8 carbons, a chloromethyl group, a bromomethyl group, a bromoethyl group, a methoxymethyl group, a phenyl group, or a chlorophenyl group, and X denotes O or S. 
     
     
       8. The photosensitive resin composition according to  claim 1 , wherein Component A above is an oxime sulfonate compound represented by any one of Formulae (17) to (22) below 
       
         
           
           
               
               
           
         
       
       wherein in Formulae (17) to (22) R 1  denotes an alkyl group, an aryl group, or a heteroaryl group, R 8  denotes a hydrogen atom or a methyl group, R 10  denotes a hydrogen atom or a bromine atom, R 11  denotes an unsubstituted alkyl group having 1 to 8 carbons, a halogen atom, a chloromethyl group, a bromomethyl group, a bromoethyl group, a methoxymethyl group, a phenyl group, or a chlorophenyl group, R 12  denotes a hydrogen atom, a halogen atom, a methyl group, or a methoxy group, and R 13  denotes an unsubstituted alkyl group having 1 to 8 carbons, a chloromethyl group, a bromomethyl group, a bromoethyl group, a methoxymethyl group, a phenyl group, or a chlorophenyl group. 
     
     
       9. An oxime sulfonate compound represented by Formula (2), Formula (3), or Formula (4) below 
       
         
           
           
               
               
           
         
       
       wherein in Formula (2) to Formula (4) R 1  denotes an alkyl group, an aryl group, or a heteroaryl group, each R 2  independently denotes a hydrogen atom, an alkyl group, an aryl group, or a halogen atom, each R 6  independently denotes a halogen atom, an alkyl group, an alkyloxy group, a sulfonic acid group, an aminosulfonyl group, or an alkoxysulfonyl group, X denotes O or S, n denotes 1 or 2, and m denotes an integer of 0 to 6, provided that of two or more R 2 s present in the compound, at least one is an alkyl group, an aryl group, or a halogen atom. 
     
     
       10. The oxime sulfonate compound according to  claim 9 , wherein it is represented by any one of Formulae (5) to (10) below 
       
         
           
           
               
               
           
         
       
       wherein in Formulae (5) to (10) R 1  denotes an alkyl group, an aryl group, or a heteroaryl group, R 2  denotes a hydrogen atom, an alkyl group, an aryl group, or a halogen atom, each R 6  independently denotes a halogen atom, an alkyl group, an alkyloxy group, a sulfonic acid group, an aminosulfonyl group, or an alkoxysulfonyl group, R 7  denotes an alkyl group, an aryl group, or a halogen atom, R 8  denotes a hydrogen atom or a methyl group, R 9  denotes a hydrogen atom, an alkyl group, or an aryl group, X denotes O or S, and m denotes an integer of 0 to 6, provided that in Formula (6), Formula (8), and Formula (10) not all of R 2 , R 8 , and R 9  are hydrogen atoms. 
     
     
       11. The oxime sulfonate compound according to  claim 10 , wherein it is represented by any one of Formulae (11) to (16) below 
       
         
           
           
               
               
           
         
       
       wherein in Formulae (11) to (16) R 1  denotes an alkyl group, an aryl group, or a heteroaryl group, R 8  denotes a hydrogen atom or a methyl group, R 10  denotes a hydrogen atom or a bromine atom, R 11  denotes an unsubstituted alkyl group having 1 to 8 carbons, a halogen atom, a chloromethyl group, a bromomethyl group, a bromoethyl group, a methoxymethyl group, a phenyl group, or a chlorophenyl group, R 12  denotes a hydrogen atom, a halogen atom, a methyl group, or a methoxy group, R 13  denotes an unsubstituted alkyl group having 1 to 8 carbons, a chloromethyl group, a bromomethyl group, a bromoethyl group, a methoxymethyl group, a phenyl group, or a chlorophenyl group, and X denotes O or S. 
     
     
       12. The oxime sulfonate compound according to  claim 11 , wherein it is represented by any one of Formulae (17) to (22) below 
       
         
           
           
               
               
           
         
       
       wherein in Formulae (17) to (22) R 1  denotes an alkyl group, an aryl group, or a heteroaryl group, R 8  denotes a hydrogen atom or a methyl group, R 10  denotes a hydrogen atom or a bromine atom, R 11  denotes an unsubstituted alkyl group having 1 to 8 carbons, a halogen atom, a chloromethyl group, a bromomethyl group, a bromoethyl group, a methoxymethyl group, a phenyl group, or a chlorophenyl group, R 12  denotes a hydrogen atom, a halogen atom, a methyl group, or a methoxy group, and R 13  denotes an unsubstituted alkyl group having 1 to 8 carbons, a chloromethyl group, a bromomethyl group, a bromoethyl group, a methoxymethyl group, a phenyl group, or a chlorophenyl group. 
     
     
       13. A photosensitive resin composition comprising:
 (Component A′) an oxime sulfonate compound represented by Formula (1′); 
 (Component B′) a (meth)acrylic copolymer comprising a constituent unit having an acid-decomposable group that is decomposed by an acid to form a carboxyl group, and 
 (Component C) a solvent 
 
       
         
           
           
               
               
           
         
       
       wherein in Formula (1′) R 1  denotes an alkyl group, an aryl group, or a heteroaryl group, Ar denotes an o-arylene group or an o-heteroarylene group, X denotes O or S, and n denotes 1 or 2. 
     
     
       14. The photosensitive resin composition according to  claim 13 , wherein Component B′ above is a (meth)acrylic copolymer comprising a constituent unit having a carboxyl group that is protected by an acetal group. 
     
     
       15. The photosensitive resin composition according to  claim 13 , wherein Component A′ above is an oxime sulfonate compound represented by Formula (2′), Formula (3′), or Formula (4′) 
       
         
           
           
               
               
           
         
       
       wherein in Formula (2′) to Formula (4′) R 1  denotes an alkyl group, an aryl group, or a heteroaryl group, each R 2  independently denotes a halogen atom, an alkyl group, an alkyloxy group, a sulfonic acid group, an aminosulfonyl group, or an alkoxysulfonyl group, X denotes O or S, n denotes 1 or 2, and m denotes an integer of 0 to 6. 
     
     
       16. The photosensitive resin composition according to  claim 13 , wherein Component B′ above further comprises a constituent unit having a functional group that can react with a carboxyl group to form a covalent bond. 
     
     
       17. A method for forming a cured film, the method comprising:
 (1) an application step of applying the photosensitive resin composition according to  claim 1  onto a substrate; 
 (2) a solvent removal step of removing the solvent from the photosensitive resin composition that has been applied; 
 (3) an exposure step of exposing to actinic radiation the photosensitive resin composition that has been applied; 
 (4) a development step of developing the exposed photosensitive resin composition by means of an aqueous developer; and 
 (5) a post-baking step of thermally curing the developed photosensitive resin composition. 
 
     
     
       18. A cured film formed by applying at least one of light and heat to the photosensitive resin composition according to any one of  claim 1 . 
     
     
       19. The cured film according to  claim 18 , wherein it is an interlayer insulating film. 
     
     
       20. An organic EL display device comprising the cured film according to  claim 18 . 
     
     
       21. A liquid crystal display device comprising the cured film according to  claim 18 .